Metaperiodic acid → HCID 68128587, compound

Participants

Reaction Steps

A solution of 20.1 g of crude 9-fluoro-11β ,17,21-trihydroxy-16α-(oxiranyl-methoxy)pregn-4-ene-3,20 -dione, 21-acetate in 300 ml of tetrahydrofuran is stirred with a solution of 30 g of periodic acid in 75 ml of water for 6 3/4 hours. The solution is diluted with water and extracted with chloroform. The chloroform extract was washed with 5% sodium bicarbonate solution, dried, and evaporated in vacuo to give 18.2 g of crude product. This material is dissolved in 60 ml of dichloromethane and chromatographed on a 450 g-silica gel column. Fractions of 250 ml are collected as the column is eluted with 3 liters of dichloromethane, 3 liters of chloroform, and then 3 liters of 19:1 chloroform-ethyl acetate. Fractions 17-21 are combined and evaporated in vacuo to give 4.4 g of 16α-allyloxy-9-fluoro-11β ,17,21-trihydroxypregn-4-ene-3,20-dione, 21-acetate.

Provenance & Evidence